Israel rods



are not salts, but amid-like bodies.

NITE- STATES PROCESS OF MAKING SALTS OF PARAM IDOPHENOL.

SPECIFICATION forming part of Letters Patent No. 602,109, dated April 12, 1898.

Application filed June 19,1895. Serial No. 553,297- (Specimens) Patented in England June 8, 1895, No. 11,288; in Belgium June 10, 1895,11'0. 116,014; in Austria, June 10,1895,No-45/3,366,' in France June 11, 1895, No. 248,069, and in Hungary June 14,1895,N0.4,805.

To all whom it mag concern.-

Be it known that I, ISRAEL Roos, chemist, a subject of the German Emperor, residing at Frankfort-on-the-Main, in the Kingdom of Prussia and German Empire, have invented certain new and useful Improvements in the Manufacture of Citrates, Tartrates, and Amygdalates of Paranisidin and Paraphenetidin; and I do hereby declare the following to be a full, clear, and exact description of the invention, such as will enable others skilled in the art to which it appertains to make and use the same.

This invention relates to the manufacture of salts formed bythe action of citric acid upon the alkyl ether of paramidophenol, and particularly with paraphenetidin an'd paranisidin.

For this process a patent has been granted in England, No. 11,288, dated June 8, 1895; in Belgium, No. 116,014, dated June 10, 1895; in France, No. 248,069, dated June 11,1895; in Hungary, No. 4,805, dated June 14, 1895, and in Austria, No. 45 3,366, dated June 10, 1895.

The new salts are obtained by bringing together one molecule of citric acid and one molecule of amidophenol ether in an appropriate solvent like alcohol.

The reaction which takes place is explained by the following equation:

0 11 0, NH,o,H,o alkyl o,H,o,.NH,o,H oa1k 1. Citric acid. Amidophenol ether. Citrate of amidophenolether.

An excess of the base does not alter the reaction, as it-will remain in the solvent. The salts thus formed, which may be called primary citrates of amidophenol ether, having the general formula G I-I O .NH C H O alkyl,

are new and not identical with other alreadyknown compounds which are obtained by heating citric acid with amidophenol ethers. These latter compounds, the constitution of which is expressed by the'equation O H O NH CH 0 alkyl QE 0 .N'HC H Oalkyl-l-H O Citiic acid. Amiclophe nolether. (litry la midopllenol ether. 2

One of these amid-like compounds formed by heating citric acid with phenetidin is apolysin, the composition of which corresponds to the 5 formula By heating citric acid (one molecule) and amidophenol ethyl ether (one molecule) water splits off and apolysin is obtained; but by mixing the said components in a solvent a salt is obtained, which is the object of this application, and this salt is already on the marric acid. They are very soluble in water and less so in alcohol. They have a meltingpoint of 186 centigrade. The citrate of paranisidin (C I-I O,.NH O H OOH may be obtained in a similar manner. The meltingpoint of 'this latter salt is 186 centigrade.

All citrates of alkyl ethers of paramidophenols are decomposed at a low temperature by the action of alkalies, the components citric alkali and alkyl ethers of paramidophenol being reproduced. All these citrates are very soluble in water, less so in alcohol, and

are very nearly insoluble in petroleum ether and in benzene.

The citrates of amidophenol alkyl ester are employed in cases of rheumatic and feverish illnesses at doses from 0.6 to two grains per diem. 8

Having now described my invention, what I claim is- 1. Process for the. manufacture of primary citrates of alkyl ethers of paramidophenols, which consists in dissolving molecular quantio ties of citric acid and amidophenol alkyl ether in a suitable solvent, such as alcohol and.- crystallizing out the salt thus obtained, substantially as described.

2. As new products of manufacture, the primary salts of citric acid with alkyl ethers of paramiclophenol composed according to the formula c n ommc fi o alkyl, being white orystallizing compounds, melting 5 at 186 to 187 centigrade, easily soluble in Water, less soluble in alcohol and almost insoluble in petroleum ether and benzene.

In testimony whereof I have affixed my signature in presence of two witnesses.

ISRAEL ROOS.

l/Vitnessesz JEAN GRUND, FRANK H. MASON. 

